[2,2-dimethylpropanoyloxymethoxy-(1-hydroxy-2-oxo-3-piperidyl)phosphoryl]oxymethyl 2,2-dimethylpropanoate

ID: ALA4647008

Chembl Id: CHEMBL4647008

PubChem CID: 122540908

Max Phase: Preclinical

Molecular Formula: C17H30NO9P

Molecular Weight: 423.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)C(=O)OCOP(=O)(OCOC(=O)C(C)(C)C)C1CCCN(O)C1=O

Standard InChI:  InChI=1S/C17H30NO9P/c1-16(2,3)14(20)24-10-26-28(23,12-8-7-9-18(22)13(12)19)27-11-25-15(21)17(4,5)6/h12,22H,7-11H2,1-6H3

Standard InChI Key:  TVFIFFUSHZDTKT-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4647008

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 423.40

Molecular Weight (Monoisotopic): 423.1658

AlogP: 2.69

#Rotatable Bonds: 7

Polar Surface Area: 128.67

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.27

CX Basic pKa: ┄

CX LogP: 2.86

CX LogD: 2.80

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.28

Np Likeness Score: 0.37

References

1. Yan VC, Yang KL, Ballato ES, Khadka S, Shrestha P, Arthur K, Georgiou DK, Washington M, Tran T, Poral AH, Pham CD, Yan MJ, Muller FL..  (2020)  Bioreducible Phosphonoamidate Pro-drug Inhibitor of Enolase: Proof of Concept Study.,  11  (7): [PMID:32676158] [10.1021/acsmedchemlett.0c00203]

2. Yan VC,Pham CD,Arthur K,Yang KL,Muller FL.  (2020)  Aliphatic amines are viable pro-drug moieties in phosphonoamidate drugs.,  30  (24): [PMID:33130289] [10.1016/j.bmcl.2020.127656]

3. Yan VC, Pham CD, Ballato ES, Yang KL, Arthur K, Khadka S, Barekatain Y, Shrestha P, Tran T, Poral AH, Washington M, Raghavan S, Czako B, Pisaneschi F, Lin YH, Satani N, Hammoudi N, Ackroyd JJ, Georgiou DK, Millward SW, Muller FL..  (2022)  Prodrugs of a 1-Hydroxy-2-oxopiperidin-3-yl Phosphonate Enolase Inhibitor for the Treatment of ENO1-Deleted Cancers.,  65  (20.0): [PMID:36251833] [10.1021/acs.jmedchem.2c01039]

Source

Source(1):

• Scientific Literature